trans-5,5-bis(phenylsulfonyl)-2-pentene | 107735-50-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-5,5-bis(phenylsulfonyl)-2-pentene
• 英文别名: (E)-5,5-bis(phenylsulfonyl)-2-pentene；1,1-bisbenzenesulfonyl-3E-pentene；[(E)-1-(benzenesulfonyl)pent-3-enyl]sulfonylbenzene
• CAS: 107735-50-2
• 化学式: C₁₇H₁₈O₄S₂
• 分子量: 350.46
• InChiKey: QBALMNLFHSAOQA-NSCUHMNNSA-N

物化性质

• 熔点：
  88 °C
• 沸点：
  570.8±50.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-5,5-bis(phenylsulfonyl)-2-pentene 在 aluminium amalgam 、 potassium tert-butylate 、 sodium hydride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.25h， 生成 2E,4E-undecadiene
  参考文献：
  名称：

  用砜XLIV合成通过从E均烯丙基砜中消除苯磺酸来立体选择性制备EE 1,3-二烯。

  摘要：

  制备纯的E和Z均烯丙基1，1-二砜，然后立体选择性地还原一个磺酰基部分，分别得到纯的E和Z均烯丙基砜，在THF中用tBuOK基本消除，得到相应的1，3-二烯，收率良好。该反应在E均烯丙基砜的情况下具有高度立体选择性，已被用于合成（8E，10E）8,10-十二碳烯醇和（9E）9,11-十二碳烯醇昆虫信息素组分。

  DOI：

  10.1016/s0040-4020(01)82061-5
• 作为产物：
  描述：

  2-丁烯基溴 、 双苯磺酸甲烷 在 sodium hydride 作用下， 生成 trans-5,5-bis(phenylsulfonyl)-2-pentene
  参考文献：
  名称：

  (Phenylsulfonyl)allenes as Substrates for Cycloaddition Reactions: Intramolecular Cyclizations onto Unactivated Alkenes

  摘要：

  The reaction of a series of allyl-substituted bis(phenylsulfonyl)methanes or dimethyl malonates with 2,3-bis(phenylsulfonyl)-1,3-butadiene in the presence of base afforded alkenyl-substituted allenes in good yield. The reaction proceeds by initial attack of the soft carbanion onto the terminal position of the diene, and this is followed by PhSO(2)(-) elimination to give the phenylsulfonyl-substituted allene. Themal [2 + 2]-cycloaddition proceeded across the C-1-C-2 double bond of the allene with completely sterospecificity. Stepwise bonding prefers to occur in a 1,6-exo manner rather than in a 1,7-endo fashion. Substitution at the 7-position of the pi-bond causes a crossover in the regioselectivity of the [2 + 2]-cycloaddition process. All products can be rationalized by a mechanism which includes an initial carbon-carbon bond formation involving the central allene carbon to give a diradical intermediate. The product distribution is then determined by the substitution pattern of the alkene and the fate of the diradical intermediate.

  DOI：

  10.1021/ja00132a005

文献信息

• Peri and stereoselectivity effects in the intramolecular [2+2]-cycloaddition reaction of phenylsulfonyl-substituted allenes
  作者：Albert Padwa、Michelle A. Filipkowski、Michael Meske、Scott H. Watterson、Zhijie Ni

  DOI：10.1021/ja00062a054

  日期：1993.5
• Methyl effects in the cyclization of .gamma.-epoxy bis-sulfones
  作者：Fabio Benedetti、Federico Berti、Silvio Fabrissin、Teresa Gianferrara、Amerigo Risaliti

  DOI：10.1021/jo00011a017

  日期：1991.5

  A quantitative study on the effects of methyl and gem-dimethyl groups in the intramolecular ring opening of epoxides by bis-sulfonyl carbanions is reported for the formation of cyclopropanes. Reaction rates are increased by methyl groups on the chain connecting the nucleophile with the oxirane and depressed by methyl substitution in the epoxide ring. When gem-dimethyl groups are present on the epoxide, ring opening is apparently inhibited. It will be shown that in this case the reaction is reversible and the apparent stabilization of the gem-dimethyl-substituted oxirane is actually due to a combination of effects on both the forward and the reverse reactions. On the basis of current theories on intramolecular reactions, it is suggested that release of ground-state strain and van der Waals repulsions in the transition state can account for the observed reactivity.
• BENEDETTI, FABIO;BERTI, FEDERICO;FABRISSIN, SILVIO;GIANFERRARA, TERESA;RI+, J. ORG. CHEM., 56,(1991) N1, C. 3530-3537
  作者：BENEDETTI, FABIO、BERTI, FEDERICO、FABRISSIN, SILVIO、GIANFERRARA, TERESA、RI+

  DOI：——

  日期：——
• PENHOAT C. H. DU; JULIA M., TETRAHEDRON, 42,(1986) N 17, 4807-4816
  作者：PENHOAT C. H. DU、 JULIA M.

  DOI：——

  日期：——
• Synthesis with sulfones XLIV Stereoselective preparation of EE 1,3-dienes by elimination of benzenesulfinic acid from E homoallylic sulfones.
  作者：C.Herve Du Penhoat、M. Julia

  DOI：10.1016/s0040-4020(01)82061-5

  日期：1986.1

  The preparation of pure E and Z homoallylic 1,1-disulfones followed by the stereoselective reduction of one sulfonyl moiety afforded pure E and Z homoallylic sulfones respectively Basis elimination with tBuOK in THF gave the corresponding 1,3-dienes in good yield. This reaction, highly stereoselective in the case of E homoallylic sulfones, has been used in the synthesis of (8E,10E) 8,10-dodecadienol

  制备纯的E和Z均烯丙基1，1-二砜，然后立体选择性地还原一个磺酰基部分，分别得到纯的E和Z均烯丙基砜，在THF中用tBuOK基本消除，得到相应的1，3-二烯，收率良好。该反应在E均烯丙基砜的情况下具有高度立体选择性，已被用于合成（8E，10E）8,10-十二碳烯醇和（9E）9,11-十二碳烯醇昆虫信息素组分。